The invention relates to 4-trifluoromethyl-3-oxazolylpyridines, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.
It is already known that suitably substituted pyridines have acaricidal and insecticidal action. Thus, WO 95/07891 discloses pyridines which carry, in the 4 position, a cycloalkyl radical which is attached via a heteroatom and, in the 3 position, a group of various substituents. However, the desired action with respect to harmful organisms is not always satisfactory. Additionally, these compounds frequently have undesirable toxicological properties with respect to mammals and aquatic animals.
International Application WO-A-98/57969, which is no prior publication, proposes 4-haloalkyl-3-heterocyclylpyridines and -pyrimidines for use as pesticides.
It was an object of the present invention to provide compounds having good insecticidal and acaricidal properties, combined with low toxicity with respect to mammals and aquatic animals.
It has now been found that compounds of the formula (I), if desired also as salts, have, compared with the prior-art compounds, a broader activity spectrum with respect to animal pests, combined with more favorable toxicological properties with respect to mammals and aquatic animals.
Accordingly, the invention provides compounds of the formula (I), 
where the symbols and indices are as defined below:
m is 0 or 1;
R1 and R2 are
a) H, CH3, xe2x80x94C2H5, xe2x80x94CH2xe2x80x94CH2xe2x80x94CH3, xe2x80x94CH2(CH3)2 or cyclopropyl or
b) xe2x80x94CH3, xe2x80x94CH2XR3, xe2x80x94CHY, xe2x80x94CO2R4 or xe2x80x94CONR5R6,
where in each case one of the radicals R1, R2 is of the group a and the other is of the group b;
X is O, S, SO, SO2 or NR7;
Y is O, BR2, xe2x80x94Oxe2x80x94(CH2)2xe2x80x94Oxe2x80x94, ((C1-C4)-alkoxy)2, ((C1-C4)-alkylthio)2, Vxe2x80x94(CH2)2 or 3xe2x80x94V, where V=O, S, where an H atom is optionally replaced by (C1-C4) alkyl;
R3 is R8, COR9, CO2R10, CONR11R12 or, if X is O or NR7, SO2R13,
R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 are identical or different and are independently of one another H, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, aryl or heterocyclyl, where each of the eight last-mentioned groups is unsubstituted or mono- or polysubstituted, and where, if appropriate, in each case R5 and R6 and R11 and R12 together are xe2x80x94(CH2)4xe2x80x94, xe2x80x94(CH2)5xe2x80x94, xe2x80x94(CH2)2xe2x80x94Oxe2x80x94(CH2)2xe2x80x94 or xe2x80x94(CH2)2xe2x80x94NR4xe2x80x94(CH2)2;
with the proviso, that the compounds in which
R1=CO2C2H5 and R2=H,
R1=H and R2=CH2 NHC6H5,
R1=CH3 and R2=CO2H,
R1=CH3 and R2=CO2C2H5,
R1=CH3 and R2=CON(CH3)2,
R1=CH(CH3)2 and R2=CO2H,
R1=CH(CH3)2 and R2=CO2C2H5 are not included.
Preferred compounds of the formula (I) are, for example,
1. compounds in which R1 is H and R2 is a radical of the group b;
2. compounds in which R1 is a radical of the group b and R2 is H,
3. compounds in which R1 is a radical of the group a, with the exception of hydrogen, and R2 is a radical of the group b.
m is preferably 0.
If m=1 and R1 or R2=CH2S(O)nR3, n is preferably 2.
From the group a, H, CH3 and cyclopropyl are preferred. From the group b, CH2XR3 and xe2x80x94CONR5R6 are preferred.
R4 . . . 13 are preferably
a) H, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, where the six last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of:
halogen, cyano, citro, hydroxyl, xe2x80x94C(xe2x95x90W)R14, xe2x80x94C(xe2x95x90NOR10)R14, xe2x80x94C(xe2x95x90NNR142)R14, xe2x80x94C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR142, xe2x80x94OC(xe2x95x90W)R14, xe2x80x94OC(xe2x95x90W)OR14, xe2x80x94NR5C(xe2x95x90W)R14, xe2x80x94N[C(xe2x95x90W)R14]2, xe2x80x94NR14C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR14xe2x80x94NR142, xe2x80x94C(xe2x95x90W)NR14xe2x80x94NR14[C(xe2x95x90W)R15], xe2x80x94NR14xe2x80x94C(xe2x95x90W)NR142, xe2x80x94NR14xe2x80x94NR14C(xe2x95x90W)R14, xe2x80x94NR14xe2x80x94N[C(xe2x95x90W)R14]2, xe2x80x94N[(Cxe2x95x90W)R14]xe2x80x94NR142, xe2x80x94NR14xe2x80x94NR14[(Cxe2x95x90W)WR14], xe2x80x94NR14(Cxe2x95x90NR14)R14, xe2x80x94NR14(Cxe2x95x90NR14)xe2x80x94NR142, xe2x80x94Oxe2x80x94NR142, xe2x80x94Oxe2x80x94NR14(Cxe2x95x90W)R14, xe2x80x94SO2NR142, xe2x80x94NR14SO2R14, xe2x80x94SO2OR14, xe2x80x94OSO2R14, xe2x80x94OR14, xe2x80x94NR142, xe2x80x94SR14, xe2x80x94SiR143, xe2x80x94SeR14, xe2x80x94PR142, xe2x80x94P(xe2x95x90W)R142, xe2x80x94SOR14, xe2x80x94SO2R14, xe2x80x94PW2R142, xe2x80x94PW3R142, aryl and
heterocyclyl,
the two last-mentioned radicals of which are unsubstituted or substituted by one or more radicals from the group consisting of
(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, (C1-C6)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, halogen, xe2x80x94OR14, xe2x80x94NR142, xe2x80x94SR14, xe2x80x94SiR143, xe2x80x94C(xe2x95x90W)R14, xe2x80x94C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR142, xe2x80x94SOR14, xe2x80x94SO2R14, nitro, cyano and hydroxyl,
b) aryl, which is unsubstituted or substituted by one or more radicals from the group consisting of (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl, where these six abovementioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of
halogen, cyano, nitro, xe2x80x94C(xe2x95x90W(R14, xe2x80x94C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR142, xe2x80x94OR14, xe2x80x94NR142, xe2x80x94SR14, xe2x80x94SOR14 and xe2x80x94SO2R14, halogen, cyano, nitro, xe2x80x94C(xe2x95x90W)R14, xe2x80x94Cxe2x95x90NOR10)R14, xe2x80x94C(xe2x95x90NNR142)R14, xe2x80x94C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR142, xe2x80x94OC((xe2x95x90W)R14, xe2x80x94OC(xe2x95x90W)OR14, xe2x80x94NR14C(xe2x95x90W)R14, xe2x80x94[C(xe2x95x90W)R14]2, xe2x80x94NR14C(xe2x95x90W)OR14, xe2x80x94OR14, xe2x80x94NR142, xe2x80x94SR14, xe2x80x94SiR143, xe2x80x94PR142, xe2x80x94SOR14, xe2x80x94SO2R14, xe2x80x94PW2R142 and xe2x80x94PW3R142,
c) heterocyclyl which is unsubstituted or substituted by one or more radicals from the group consisting of
(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl,
where these six abovementioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of
halogen, cyano, nitro, xe2x80x94C(xe2x95x90W)R14, xe2x80x94C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR142), OR14, xe2x80x94NR142, xe2x80x94SR14, xe2x80x94SOR14 and xe2x80x94SO3R14,
halogen, cyano, nitro, xe2x80x94C(xe2x95x90W(R14, xe2x80x94C(xe2x95x90NOR10)R14, xe2x80x94C(xe2x95x90NNR142)R14, xe2x80x94C(xe2x95x90W)OR14, xe2x80x94C(xe2x95x90W)NR142, xe2x80x94OC(xe2x95x90W)R14, xe2x80x94OC(xe2x95x90W)OR14, xe2x80x94NR14C(xe2x95x90W)R14, xe2x80x94[C(xe2x95x90W)R14]2, xe2x80x94NR14C(xe2x95x90W)OR14, xe2x80x94OR14xe2x80x94NR142, xe2x80x94SR14, SiR143, xe2x80x94PR142, xe2x80x94SOR14, xe2x80x94SO2R14, xe2x80x94PW2R14 and xe2x80x94PW3R142,
W is O or S;
R14 is identical or different and is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-(C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)alkyl, (C3-C8)-cycloalkyl-(C2-C4)alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, (C1-C6)-alkyl-(C3-C8)-cycloalkyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenyl, (C2-C6)-alkenyl-(C4-C8)cycloalkenyl, where the fourteen last-mentioned radicals are unsubstituted or substituted by one or more, preferably 1 to 3, radicals from the group consisting of
halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C2-C4)-alkenyloxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyloxy, (C1-C6)-alkyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkenyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkynyl-(C3-C8)-cycloalkoxy, (C1-C6)-alkyl-(C4-C8)-cycloalkenyloxy, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyloxy, (C1-C4)-alkoxy-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C2-C6)-alkenyloxy, carbamoyl, (C1-C6)-mono- or -dialkylcarbamoyl, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C3-C8)-mono- or dicycloalkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C6)-alkanoyloxy, (C3-C8)-cycloalkanoyloxy, (C1C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkanamido, (C1-C6)-haloalkanamido, (C2-C6)-alkanamido, (C3-C8)-cycloalkanamido, (C3-C8)-cycloalkyl-(C1-C4)-alkanamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkylthio, (C4-C8)-halocycloalkenyllthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl-(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkoynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalkylsulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfinyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl,
(C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8) -halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkylamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, where the cyclic moiety of the fourteen last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of
halogen, cyano, nitro, amino, hydroxyl, thio, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylamino, (C1C4)-haloalkylamino formyl and (Cl-C4)-alkanoyl,
aryl, 5- or 6-membered heteroaromatic, where the two last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of
halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, carbamoyl, (C1-C6)-mono- or -dialkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkanoyloxy, (C1-C6)-mono- or -dihaloalkylcarbamoyl, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkanamido, (C1-C6)-haloalkanamido, (C2-C6)-alkanamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkylthio, (C4-C8)-halocycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalkylsulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkylamino and (C4-C8)-halocycloalkenylamino.
R4 . . . 14 are particularly preferably identical or different and are H, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, aryl or heterocyclyl, where each of the seven last-mentioned groups is unsubstituted or substituted by one or more radicals from the group consisting of halogen, preferably F, (C1-C4)-alkoxy, (C1-C4)-alkylthio, NRxe2x80x2xe2x80x94COxe2x80x94(C1-C6)-alkyl, where Rxe2x80x2=H or (C1-C4)-alkyl.
Particular preference is given to the following groups of compounds of the formula (I) a-f 
Very particular preference is given to compounds of the formula Ia1-Ia12 
Very particular preference is furthermore given to compounds of the formula 1b1 to 1b12: 
The symbols in the formulae Ia-f and 1a-12, respectively, and Ib1-12 have the abovementioned meanings and preferences.
The term xe2x80x9chalogenxe2x80x9d includes fluorine, chlorine, bromine and iodine.
The term xe2x80x9c(C1-C4)-alkylxe2x80x9d is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term xe2x80x9c(C1-C6)-alkylxe2x80x9d includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term xe2x80x9c(C1-C10)-alkylxe2x80x9d is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2decyl radical.
xe2x80x9c(C1-C4)-Haloalkylxe2x80x9d is to be understood as an alkyl group mentioned under the term xe2x80x9c(C1-C4)-alkylxe2x80x9d in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably chlorine or fluorine, such as, for example, the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.
xe2x80x9c(C1-C4)-Alkoxyxe2x80x9d is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term xe2x80x9c(C1-C4)-alkylxe2x80x9d. The alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.
The terms xe2x80x9calkenylxe2x80x9d and xe2x80x9calkynylxe2x80x9d having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. xe2x80x9c(C2-C4)-Alkenylxe2x80x9d is thus, for example, the vinyl, allyl, 2-methyl-2-propenyl or 2-butenyl group; xe2x80x9c(C2-C6)-alkenylxe2x80x9d denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. xe2x80x9c(C2-C4)-Alkynylxe2x80x9d is, for example, the ethynyl, propargyl, 2-methyl-2-propynyl or 2-butynyl group. xe2x80x9c(C2-C6)-Alkynylxe2x80x9d is to be understood as the abovementioned radicals and, for example, the 2-pentynyl or the 2-hexynyl group and xe2x80x9c(C2-C10)-alkynylxe2x80x9d is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.
xe2x80x9c(C3-C8)-Cycloalkylxe2x80x9d denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.
The term xe2x80x9c(C3-C8)-cycloalkyl-(C1-C4)-alkyl xe2x80x9d is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term xe2x80x9c(C1-C6)-alkyl-(C3-C8)-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.
xe2x80x9c(C1-C4)Alkoxy-(C1-C6)-alkyloxyxe2x80x9d is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.
xe2x80x9c(C3-C8)-Cycloalkoxyxe2x80x9d or xe2x80x9c(C3-C8)-cycloalkylthioxe2x80x9d is to be understood as one of the abovementioned (C3-C8)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.
xe2x80x9c(C3-C8)Cycloalkyl-(C1-C6)-alkoxyxe2x80x9d is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group.
The term xe2x80x9c(C1-C4)-alkyl-(C3-C8)-cycloalkoxyxe2x80x9d is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.
xe2x80x9c(C1-C6)-Alkylthioxe2x80x9d is an alkylthio group whose hydrocarbon radical has the meaning given under the term xe2x80x9c(C1-C6)-alkylxe2x80x9d.
Correspondingly, xe2x80x9c(C1-C6)-alkylsulfinylxe2x80x9d is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and xe2x80x9c(C1-C6)-alkylsulfonylxe2x80x9d is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.
xe2x80x9c(C1-C6)-Alkylaminoxe2x80x9d is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.
The term xe2x80x9c(C1-C6)-mono- or -dialkylcarbamoylxe2x80x9d is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term xe2x80x9c(C1-C6-alkyl)xe2x80x9d and which, in the case of two hydrocarbon radicals, may be identical or different.
Correspondingly, xe2x80x9c(C1-C6)-dihaloalkylcarbamoylxe2x80x9d is a carbamoyl group which carries two (C1-C6)-haloalkyl radicals in accordance with the above definition or one (C1-C6)-haloalkyl radical and one (C1-C6)-alkyl radical in accordance with the above definition.
xe2x80x9c(C1-C6)-Alkanoylxe2x80x9d is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.
The term xe2x80x9carylxe2x80x9d is to be understood as an carbocyclic aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, for example phenyl, naphthyl or biphenylyl, preferably phenyl.
The term xe2x80x9cheterocyclylxe2x80x9d preferably denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical or different atoms from the group consisting of nitrogen, sulfur or oxygen, two oxygen atoms, however, not being allowed to be directly adjacent to one another and at least one carbon atom having to be present in the ring, for example a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term xe2x80x9cheteroaromaticxe2x80x9d thus embraces, from among the meanings mentioned above under xe2x80x9cheterocyclylxe2x80x9d, in each case the fully unsaturated aromatic heterocyclic compounds.
Heterocyclyl is particularly preferably a saturated, partially saturated or aromatic ring system having 3 to 6 ring members and 1 to 4 heteroatoms from the group consisting of O, S and N.
Heterocyclyl is very particularly preferably a radical of pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane and oxetane.
xe2x80x9cAryl-(C1-C4)-alkoxyxe2x80x9d is an aryl radical which is attached via a (C1-C4)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical. xe2x80x9cArylthioxe2x80x9d is an aryl radical attached via a sulfur atom, for example the phenylthio or the 1- or 2-naphthylthio radical. Correspondingly, xe2x80x9caryloxyxe2x80x9d is, for example, the phenoxy or 1- or 2-naphthyloxy radical.
xe2x80x9cAryl-(C1-C4)-alkylthioxe2x80x9d is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.
The term xe2x80x9c(C1-C6)-trialkylsilylxe2x80x9d denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly xe2x80x9caryl-(C1-C6)-dialkylsilylxe2x80x9d is a silicon atom which carries one aryl radical and two identical or different alkyl radicals in accordance with the above definition, xe2x80x9cdiaryl-(C1-C6)-alkylsilylxe2x80x9d is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and xe2x80x9ctriarylsilylxe2x80x9d is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.
Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry, for example, groups such as hydroxyl, carboxyl or other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C1-C4)-alkyl radicals and also mono-, di- and trialkanolamines of (C1-C4)-alkanols. If the compounds of the formula (I) carry, for example, groups such as amino, alkylamino or other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid and sulfuric acid and phosphoric acid, organic acids, such as acetic acid and oxalic acid and acidic salts, such as NaHSO4 and KHSO4. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.
The compounds of the formula (I) may have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. The mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods. The compounds according to the invention are prepared according to methods which are known per se from the literature, as described in standard works on organic synthesis, for example Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart.
The preparation is carried out under reaction conditions which are known and suitable for the reactions mentioned. It is also possible to employ variants which are known per se but not mentioned in more detail here.
If desired, the starting materials can also be formed in situ, such that they are not isolated from the reaction mixture but are immediately reacted further to give the compounds of the formula (I).
The present invention also relates to processes for preparing compounds of the formula (I):
Compounds of the formula (I) where R2=H can be prepared, for example, by further functionalization of compound (III) or (IV): 
The compounds (III) and (IV) are obtained, for example, by cyclizing compounds of the formula (V): 
Various cyclization procedures are known from the literature, for example
KOH/ethanol/reflux (see, for example, J. Reisch et al., Pharmazie 1992, 47, 18-20)
NaH/THF/70xc2x0 C. (see, for example, B. M. Nilsson et al., J. Heterocyclic Chem. 1989, 26, 269-275)
Hg (CH3CO2)2/glacial acetic acid/reflux (see, for example, J. Saunders et al., J. Med. Chem. 1990, 33, 1128-1130).
The starting material (V) is directly obtainable from commercially available trifluoromethylnicotinic acid and propargylamine by employing a dehydrating agent, such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-di-methylaminopropyl)carbodiimide or N,Nxe2x80x2-carbonyldiimidazole.
Compounds of the formula (I) where R1=H can be obtained, for example, by further functionalization of the compound (VI) 
Compound (VI) can be prepared, for example, in two steps by cyclization of (VII): 
where (VII) is, for example, initially treated at 40xc2x0 C. in glycol dimethyl ether with trimethylsilyl trifluoromethylsulfonate, followed by treatment with potassium tert-butoxide in tert-butanol at 0xc2x0 C. to give (VI) (see, for example, S. Swaminathan et al., Tetrahedron Lett. 1998, 39, 4769-4472).
Compound (VII) can be prepared, for example, under standard conditions by acylating ethyl 2-amino-3,3,diethoxypropionate with 4-trifluoromethyl-nicotinoyl chloride. Ethyl 2-amino-3,3-diethoxypropionate can be prepared by processes known from the literature (see, for example, S. K. Singh et al., Heterocycles 1997, 44, 379-391 or T. W. Doyle et al., Can. J. Chem. 1977, 55, 468-483).
Compounds in which R1 is a radical of the group a and R2 is of the group b can be prepared, for example, by further functionalization of compounds of the formula (VIII): 
where
R15 is CH3 or C2H5 and
R16 is CH3, C2H5, CH2xe2x80x94CH2xe2x80x94CH3, xe2x80x94CH(CH3)2 or cyclopropyl.
(VIII) can be prepared, for example, by cyclizing amides of the formula (IX). 
Suitable dehydrating agents which can be used for this purpose are, for example, inorganic acid chlorides, such as thionyl chloride or phosphoryl chloride, inorganic acids, such as sulfuric acid or phosphoric acid, or a mixture of acetic anhydride with an inorganic acid (see, for example, K. Meguro et al., Chem. Pharm. Buul.1986, 34, 2840-2851).
The compounds of formula (IX) can be prepared, for example, in a one-pot process from the corresponding xcex2-ketoester (X) and 4-trifluoromethylnicotinoyl chloride. 
The preparation of the oxime from the xcex2-ketoester with sodium nitrite in acetic acid, reduction with Zn/sulfuric acid and subsequent acylation is described, for example, in G. Erhart, Berichte 1949, 82, 60-63.
After the oxazole system has been constructed by condensation and cyclization reactions, the radicals R1 and R2 of the compounds of the formula (XL) can, if desired, be derivatized further, using the broad range of methods of organochemical synthesis familiar to the person skilled in the art.
Esters and carboxamides of the formula (I) can be obtained, for example, from compounds of the formula (XI) by methods known from the literature and familiar to the person skilled in the art, such as transesterification, aminolysis or amide formation from carboxylic acids and amines using a dehydrating agent, such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-di-methylaminopropyl)carbodiimide, N,Nxe2x80x2-carbonyldiimidazole or 2-(1H-benzotriazol-2-yl)-1,1,3,3-tetramethylammonium tetrafluoroborate. 
where
R1, R2 or R1xe2x80x2, R2xe2x80x2 have, for example, the following meanings:
R4, R5 and R6 are as defined above.
Compounds of formula (XI) where R1=CO2Et, CO2Me, CO2H; R2=H, Me, Et, n-Pr, i-Pr and c-Pr can be obtained directly by the cyclization reactions described or by hydrolysis of the esters of cyclization products.
Compound (XI) where R1=H and R2=CO2H can be prepared, for example, from compound (III) or (IV) by oxidation according to processes known from the literature.
Ethers, thioethers and amines and other derivatives of the formula (XIV) can be obtained, for example, from compounds of the formula (XIII) by reactions with appropriate nucleophiles, said reactions being known from the literature and familiar to the person skilled in the art. 
where X, R3 and R4 are as defined above.
Compounds of the formula (XIII) can be prepared from compounds of the formulae (III), (VI) and (VIII) by processes which are known from the literature and familiar to the person skilled in the art, for example 
Compounds of the formula (XIV) in which R1 or R2 is CH2XR3 where X=S or NR4, where R3 or R4=H or R3=R4=H can be reacted by methods known from the literature and familiar to the person skilled in the art to give, for example, sulfoxides, sulfones, amides and carbamates.
To synthesize compounds of the formula (I) in which m is 1, it is possible to treat compounds of the formula (I) in which m is 0 with an oxidizing agent, such as meta-chloroperbenzoic acid.
Collections of compounds of the formula (I) which can be synthesized by the abovementioned scheme may also be prepared in a parallel manner and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, the work-up or the purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S. H. DeWitt in xe2x80x9cAnnual Reports in Combinatorial Chemistry and Molecular Diversity: Automated synthesisxe2x80x9d, Volume 1, Verlag Escom 1997, pages 69 to 77.
A number of commercially available apparatuses as they are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleixcex2heim, Germany, or Firma Radleys, Shirehill, Saffron Walden, Essex, CB-11:3AZ, England may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula (I), or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.
The apparatuses mentioned lead to a modular procedure in which the individual process steps are automated, but manual operations have to be performed between the process steps. This can be avoided by employing semi-integrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.
In addition to what has been described here, compounds of the formula (I) may be prepared in part or fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin.
Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in xe2x80x9cThe Combinatorial Indexxe2x80x9d, Verlag Academic Press, 1998.
The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the xe2x80x9ctea-bag methodxe2x80x9d (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.
The preparation according to the processes described herein yields compounds of the formula (I) in the form of substance collections which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I).
The compounds of the formula (I) are suitable for controlling animal pests, in particular insects, arachnids, helminths and mollusks, very especially preferably for controlling insects and arachnids, which are encountered in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials and in the hygiene sector, and have good plant tolerance and favorable toxicity to warm-blooded species. They are active against normally sensitive and resistant species and against all or individual development stages. The abovementioned pests include:
From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.
From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgare and Porcellio scaber. 
From the order of the Diplopoda, for example, Blaniulus guttulatus. 
From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.
From the order of the Symphyla, for example, Scutigerella immaculata. 
From the order of the Thysanura, for example, Lepisma saccharina. 
From the order of the Collembola, for example, Onychiurus armatus. 
From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeira, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. 
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. 
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana. 
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conodenus spp., Melolontha melolontha, Amphirmallon solstitialis and Costelytra zealandica. 
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. 
From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.
From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. 
From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.
From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.
From the class of Bivalva, for example, Dreissena spp.
The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii) and of the genera Radopholus, such as Radopholus similis, Pratylenchus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus; 
Tylenchulus, such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus, such as Rotylencus robustus, Heliocotylenchus, such as Heliocotylenchus multicinctus, Belonoaimus, such as Belonoaimus longicaudatus, Longidorus, such as Longidorus elongatus, Trichodorus, such as Trichodorus primitivus and Xiphinema, such as Xiphinema index.
The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (blossom nematodes, such as Anguina tritici) can furthermore be controlled with the compounds according to the invention.
The invention also relates to compositions, in particular insecticidal and acaricidal compositions, which comprise one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
The compositions according to the invention in general comprise from 1 to 95% by weight the active compounds of the formula (I). They can be formulated in various ways, depending on how this is determined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore: Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.
These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kxc3xcchler, xe2x80x9cChemische Technologiexe2x80x9d [Chemical Technology], Volume 7, C. Hauser Vedag Munich, 4th Edition 1986; van Falkenberg, xe2x80x9cPesticides Formulationsxe2x80x9d, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, xe2x80x9cSpray Drying Handbookxe2x80x9d, 3rd Edition 1979, G. Goodwin Ltd. London.
The necessary formulation auxiliaries, i.e. carrier substances and/or surface-active substances, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, xe2x80x9cHandbook of Insecticide Dust Diluents and Carriersxe2x80x9d, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, xe2x80x9cIntroduction to Clay Colloid Chemistryxe2x80x9d, 2nd Edition, J. Wiley and Sons, N.Y.; Marsden, xe2x80x9cSolvents Guidexe2x80x9d, 2nd Edition, Interscience, N.Y. 1950; McCutcheon""s, xe2x80x9cDetergents and Emulsifiers Annualxe2x80x9d, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, xe2x80x9cEncyclopedia of Surface Active Agentsxe2x80x9d, Chem. Publ. Co. Inc., N.Y. 1964; Schxc3x6nfeldt, xe2x80x9cGrenzflxc3xa4chenaktive xc3x84thylenoxidadduktexe2x80x9d [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Kxc3xcchler, xe2x80x9cChemische Technologiexe2x80x9d [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.
Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2xe2x80x2-dinaphthylmethane-6,6xe2x80x2-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
Dusting powders are obtained, for example, by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophillite, or diatomaceous earth. Granules can, for example, be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granulesxe2x80x94if desired as a mixture with fertilizers.
In wettable powders, the active compound concentration is generally about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.
In addition, the active compound formulations mentioned comprise, if appropriate, particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carrier substances.
For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.
The required amount applied varies with the external conditions, such as temperature, humidity and the like. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active compound, but is preferably between 0.001 and 5 kg/ha.
The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations as mixtures with other active compounds, such as other pesticides, for example, insecticides or acaricides, attractants, sterilizing agents, nematicides, fungicides, growth-regulating substances or herbicides. The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.
Preferred partners for the mixtures are:
1. from the group of phosphorus compounds
acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, fosthiazate (ASC-66824), heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, primiphosethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, suiprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;
2. from the group of carbamates
alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;
3. from the group of carboxylic acid esters
acrinathrin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, pheothrin ((R) isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD-2344), tralomethrin, transfluthrin and zeta-cypermethrin (F-56701);
4. from the group of amidines
amitraz, chlordimeform;
5. from the group of tin compounds
cyhexatin, fenbutatin oxide;
6. others
abamectin, ABG-9008, acetamiprid, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, Bacillus thuringiensis, Beauveria bassianea, bensultap, bifenazate (D-2341), binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, chromafenozide (ANS-118), CG-216, CG-217, CG-234, A-184699, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboxamide acid ethyl ester, DDT, dicofol, diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, diofenolan, DPX-062, ernamectin-benzoate (MK-244), endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole (YI-5301), fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, flufenprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenozide (RH-0345), halofenprox (MTI-732), hexaflumuron (DExe2x80x94473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), lufenuron, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, M-020, methoxyfenozide (Intrepid, RH-2485), milbemectin, NC-196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), pyriproxyfen (S-71639), NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargite, pymethrozine, pyridaben, pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, silafluofen, silomadine (CG-177), spinosad, SU-9118, tebufenozide, tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpyrad (OMI-88), triazamate (RH-7988), triflumuron, verbutin, vertalec (Mykotal), YI-5301,
The abovementioned combination partners are known active compounds, and most of them are described in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 9th Edition (1997), British Crop Protection Council.
The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
The active compounds are used in a customary manner appropriate for the use forms.
The active compounds according to the invention are also suitable for controlling endo- and ectoparasites in the veterinary medicine field and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, potions or granules, by means of dermal use in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, and by parenteral use in the form of, for example, injection.
The novel compounds of the formula (I) can accordingly also particularly advantageously be used in livestock husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the compounds are administered orally to the animals, if appropriate in suitable formulations and if appropriate with the drinking water or feed. Since excretion in the feces takes place in an active manner, the development of insects in the feces of the animals can be prevented very easily in this way. The dosages and formulations suitable in each case depend in particular on the species and the development stage of the stock animals and also on the level of infestation, and can easily be determined and specified by the customary methods. The novel compounds can be employed in cattle, for example, in dosages of 0.01 to 1 mg/kg of body weight.
In addition to the application methods mentioned hereinabove, the active compounds of the formula (I) according to the invention also have excellent systemic action. The active compounds can therefore also be introduced into the plants via below-ground and above-ground parts of plants (root, stem, leaf), when the active compounds are applied in liquid or solid form to the immediate surroundings of the plants (for example granules in soil application, application in flooded rice fields).
Furthermore, the active compounds according to the invention are particularly useful for treating vegetative and generatative propagation stock, such as seed of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamentals, of bulbs, cuttings and tubers of other vegetatively propagated crops and ornamentals. To this end, treatment can be carried out prior to sowing or planting (for example by special seed dressing techniques, by seed dressings in liquid or solid form or by seed box treatment), during sowing or planting or after sowing or planting by special application techniques (for example seed row treatment). Depending on the application, the amount of active compound applied can vary within a relatively wide range. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area.
The compounds of the formula (I) can also be used for controlling harmful plants in crops of known genetically modified plants or of genetically modified plants still to be developed. The transgenic plants generally have particularly advantageous properties, for example resistance to certain crop protection agents, resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. Other special properties relate, for example, to the harvested product, with respect to quantity, quality, shelf-life, composition and special ingredients. Thus, transgenic plants having increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested product are known.
Preference is given to the use in economically important transgenic crops of useful and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet, rice, manioc and maize, or else crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species.
The use in transgenic crops, in particular crops with resistance to insects, is, in addition to the effects with respect to harmful organisms which can be observed in other crops, frequently associated with effects which are specific for the application in the respective transgenic crop, for example a modified or specifically widened spectrum of pests which can be controlled, or modified application rates which can be used for the application.
The invention therefore also provides the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.
The use of the compounds according to the invention comprises, in addition to direct application to the pests, any other application where the compounds of the formula (I) act on the pests. Such indirect applications may be, for example, the use of compounds which decompose or are degraded to compounds of the formula (I), for example in the soil, the plant or the pest.
Herewith, express reference is made to the content of German Patent Application 198 58 192.0, the priority of which is claimed by the present application, and to the summary; it is incorporated into this description by reference: